


my reputation's never been worse, so you must like me for me

by benwvatt



Series: each and every universe [10]
Category: Brooklyn Nine-Nine (TV)
Genre: F/M, S1 AU where Jake is undercover and Amy is an Iannucci, dianetti as a major sideplot!!! i love them, forbidden romance!!!, so much pining
Language: English
Status: In-Progress
Published: 2020-03-05
Updated: 2020-12-30
Packaged: 2021-02-28 17:01:02
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 5
Words: 10,912
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23020624
Author URL: https://archiveofourown.org/users/benwvatt/pseuds/benwvatt
Summary: A few months ago, Jake met someone who’s finally thrown him off his game. Life hasn’t exactly been the same since she left a lipstick stain, berry-pink, on his cheek.Jake Peralta meets Amy Santiago in the worst of circumstances: when he's undercover with the NYPD, trying to take down the Iannucci family.And another thing? Amy's the Iannuccis' adopted daughter.
Relationships: Jake Peralta/Amy Santiago
Series: each and every universe [10]
Series URL: https://archiveofourown.org/series/754962
Comments: 62
Kudos: 104





	1. one

He dives in headfirst, as always.

Jake Peralta thrives on impulse, translating the thready jolt of his heartbeat into a need, solid and secure before him. The only emotions worth considering are instincts. Forget overthinking, everything else be damned. Jake’s sure of what he wants, and even more so of how to achieve it. He’ll follow this newly-found lucky streak, he promises himself. He can trace its edge like a one-lane road until it trails away beneath him.

That’s what he used to think, at least.

A few months ago, Jake met someone who’s finally thrown him off his game. Life hasn’t exactly been the same since she left a lipstick stain, berry-pink, on his cheek. Jake still remembers the tender look on Amy’s face as she wiped the mark away with her thumb.

“Better now?” Amy’d asked, her voice a touch innocent as she drew her hand away to straighten the clasp of her pearl necklace.

Jake could only nod.

That’s what happens when you let someone else become the best part of your day, Jake learned. You have to surrender some of that control. You lose your impulse, in fact.

This is one situation where Jake definitely, _definitely_ can’t dive in headfirst.

* * *

Jake’s life changes on a miserable Thursday.

There are ten case files laid out over his desk, all dull enough to put him to sleep. Just this morning, he’d received a new assignment, which had turned out to be another B&E. Jake’s only been at the Nine-Nine for about a year, yet he’s used to a better caseload than _this._ Just last month, he was secondary on a serial arson case that ended with not one, but two separate arrests. (Not to brag, of course. Just stating the facts.)

Over Jake’s shoulder, his sergeant rolls his eyes. Terry Jeffords knows his brightest detective is capable of doing more than doodling airplanes on the latest CI report they’ve received. It concerns an underground poker tournament, which is allegedly connected to a smuggling operation. With any luck, this report could blow the Iannucci conspiracy wide open.

Terry clears his throat. Jake jerks his head backward, one hand smudging the wing of a pencil-sketch Boeing on the page.

“Peralta, the captain wants to see you at the end of the day.”

Jake gives a thumbs-up with a gritted smile on the side. He definitely doesn’t spend the next four hours and thirty-six minutes waiting for work to finish, and in no way does he cast casual glances back to the captain’s office. (See, that’d be anxious behavior, which he’s trying to self-manage with deep breaths and calm thinking. It’s his newest assignment from his therapist.)

The rest of the day carries on, time heavy and cumbersome as the clock ticks. A few of the officers glare at Jake during their shared lunch break, clearly oblivious to the foot-tapping racket he’s causing. After issuing a couple DUIs and passing eight misfiled traffic tickets onto the patrol officers 一 it’s been a long, sleep-deprived week for the precinct 一 five o’clock finally draws near.

Jake sees the captain at once, one-on-one. They toss around the key phrases of small talk until Holt tires of it. He begins to speak of card games gone wrong, of blood staining warehouse floors and walls a dingy brown. After a thorough description of each, Holt ties up the last two points neatly.

“The NYPD is preparing to send a detective into the Iannucci family’s operation. It’ll be a cautious undertaking.”

The captain gives a pause of reflection, then carries on. Whether it’s for Peralta’s sake or his own is undecided. Holt coughs, his chosen transition from point to point when none else presents itself.

“If you accept, you’ll need to embed yourself within the family as a regular gambler with an interest in bookkeeping.”

Jake takes a pause, then sits up straighter. “Why me?”

Holt chuckles faintly. It seems he won’t allow a smile to appear on his blank slate of a face. “A CI we’ve been working with suggested it. They’d been reading cases for a while, and recognized your badge number appearing again and again on some of your solves. You’ve been personally selected for your bravado and your record. Plus, you fit the role of a gambling addict quite well. Both my words and theirs.”

Jake pinches his mouth into a grimace. “Thanks?”

“This won’t come easily, detective. It may cost you months with the Iannuccis, or even years if need be.” The captain draws out the last few words of his sentence, as if unbelieving that Jake understands the length of a year.

Jake gulps. The risks of Holt’s proposal are clear.

“But it’ll be worth it?”

Jake’s rickety chair is uneven on the tile, and it wobbles between two distances as he waits for a reply.

After a pause, Holt clears his throat again. “We anticipate so. No guarantees, unfortunately.”

“Understood, sir.”

So, without another lost moment, caught in the moments before and after a blink, Jake Peralta agrees to follow up on CI #10’s report. Beginning next week, he’ll be investigating the Iannucci family with intent to uncover more about their smuggling ring.

* * *

Amy Santiago isn’t an Iannucci, but she might as well be. They’re like family to her. At the age of twelve, she’d chosen her last name out of a picture book, and it’d stuck. So she trundles on, a daughter claimed by joy and not by blood. She’s long since given up on the untouchable dream of _parents._ There are better uses for her time.

Amy usually spends her evenings with a glass of red wine as she pores over her precious Excel spreadsheets. If it’s a rough night, the glass will be more than half full. This is life as it should be, Amy declares: hard work and checkboxes neatly crossed in her journal. Who needs a mom and dad when you have the whole world at your fingertips, eight adoptive siblings right there by your side?

Gina Iannucci is the closest thing Amy’s ever had to a best friend. They’re sisters, never mind the arguments about who owns the green Burberry sweater and who’ll end up paying for gas this time. Gina’s always been jealous of the sugar-dusting freckles on Amy’s cheeks, and Amy secretly wishes she had Gina’s gift for cooking. It’s a give and take relationship, they’ve both known for years.

Amy and Gina spend nights in their shared bedroom talking about love and loss and sky’s-the-limit dreams. Sometimes, they stay up talking until morning. It bothers their brother David, of course, but he gets annoyed by everything. Gina says that’s what you get when you’re so tightly wound you won’t even drink coffee. Amy always giggles at that particular critique.

When Amy spills her glass of Merlot at three in the morning, Gina’s right there with balled-up paper towels and a kind word. That’s what sisters are for, she insists. Supportive ‘till the end.

That last quip, unfortunately, doesn’t do anything to soothe the worry rising in Amy’s stomach as she clicks away from Excel and onto her latest habit at 3:10 AM. With a peek, she confirms Gina’s dead asleep before carrying on.

Amy doesn’t shut her laptop screen until the sun comes up. It hurts to blink, even, which surely can’t be a good sign, and panic surges in Amy’s heart as she hears Gina begin to wake. She slams the computer closed, not wanting anyone to know what's on the screen.

What kind of daughter can _justify_ this?

An adopted one, clearly.


	2. two

**Summary for the Chapter:**

> _Gina was her sister, getting the chance to properly adore someone before Amy’d ever gone on a first date. And with a cop, no less?_
> 
> Insight on Gina and Rosa's relationship, as Jake and Amy evolve separately. The undercover mission continues.

Jake Peralta lets his career fizzle out on purpose.

It’s a lot to take at once. It’s disappointing, to be frank, to let the lights of his ambition dim like this, covered with dust and falling into the shadows. He scans through departmental emails that try to convince him of the long haul; of setting up a ruse that the Ianuccis will never suspect.

Jake takes late-night stakeouts with no chance of capture, and the goosebumps trail up his arms while he sits shotgun. After a good two or three hours without a hint of hope, Charles hits him with worried looks from the driver’s seat; Jake doesn’t dignify them with a response. So the wind whistles, unrelenting, and car alarms whine into the distance, and the night travels on. (It’ll pay off later.)

The NYPD sends orders under the dark cover of discretion, and Jake follows suit the next week. He can already feel the weight of Charles’ and Terry’s questioning glances 一 he was once their star player, yet he’s been in a slump for countless days. Jake’s intentions are hinged on victory at first, but it’s aggravating to let the winner’s vision slip through his fingers. To lose all hope of righteous credit _again._ (It’ll pay off later.)

Nights are long, shivers racing up Jake’s back, and mornings make his head throb. He sleeps late and wakes up early. He tosses back more scotch than he’d like for a Tuesday evening, letting the last drops in the bottle trickle down the edge of the glass. He lands himself in quicksand, gets reprimanded, suspended, punished 一 anything to set up the guise of aloof confidence, forced drunkenness fogging his vision.

Jake slashes his reputation to ribbons, and he’d be lying if he said it didn’t hurt.

And when he meets Amy Santiago, he wants the thrill of her attention too badly to ignore her. Jake should know better, but, somehow, he finds himself falling for her bad jokes and love of vanilla lattes. He likes her foolishly. There’s no leaving Amy’s orbit now, what with the way her eyes catch his glance again and again when he walks into a room. Jake follows every step to fall out of love with her, and not a single one works.

He curses himself out at the time.

It’ll pay off later.

* * *

_[messages, 6:29 pm]_  
**rosa:** dinner tonight?

 **gina:** you know it babe  
**gina:** WAIT nvm i’m so sorry i have a family thing  
**gina:** raf has a shipment coming in

 **rosa:** ughhhh  
**rosa:** ofc none of your brothers are allowed to meet me  
**rosa:** isn’t raf the one with the motorcycle  
**rosa:** do you know how hard it is to find fellow motorcycle enthusiasts???

 **gina:** i’m really sorry okay :(  
**gina:** but family stuff is complicated  
**gina:** remember we decided they weren’t supposed to know about us?

* * *

Gina Iannucci doesn’t like being referred to as a triple threat. It makes the false assumption that her talents are limited to three. She knows how to rig a poker game with nothing but a mechanical pencil and a nail file, for goodness’ sake. She’s been glaring down family enemies and rolling her eyes at blackmail notes, with their crumpled magazine cut-out letters, since she can remember. Games are easy to play, after all, when you’re born to play them.

Gina’s had the entire emoji keyboard memorized since she was sixteen. She snaps her gum in long conversations, she walks with reason in each jagged step, and she wears clothes that aren’t supposed to hit markets for another month. She’s got this. She always has. Gina didn’t meet anyone remotely capable of challenging her authority until Rosa Diaz traipsed into her territory and turned the tables, just like that.

Rosa made everyone around her quiet. She had a funny way of making you feel at home with her, even if you knew precisely three facts about her life (1, her name; 2, that she lived somewhere in New York; and 3, that she drove a Harley everywhere she went.) Somehow, Rosa knew how to make an entrance _and_ how to slip into rooms so softly no one would notice her. Blending into the wallpaper, falling in line with the shadows, she’d walk out before you ever knew she’d entered.

For every parlor trick up Gina’s sleeve, Rosa had two. Rosa hadn’t been born to cast her luck in the winner’s circle, but she’d learned faster than anyone else. 

Rosa was hard to characterize, the way she cherry-picked the traits she’d show the world each day. She kept entire arsenals of pick-a-topic-and-I’ll-spill-my-guts knowledge in her head: Actors in Nancy Meyers films. Every city that’s hosted the Olympics since 1964. A list of arteries in the human body, alphabetized just for kicks. Rosa would switch all the time, and Gina lived for a chase 一 the trivial pursuit of a girl.

When one cursed, the other sat, eager, and spat bitter words by her side. Together, they were two types of poison, quick and biting, indistinguishable and razorblade red beneath the light. Gina learned the common clack of Rosa’s boots, and Rosa was left with the memory Gina’s precious Chanel no. 5, the scent of petals softening the worn neckline of her shirt.

It was this trail of perfume that lingered wherever Rosa went. It sunk into the woolen collar of her jacket, kept there like a promise, melding with the faint smell of the lotion Rosa would knead into Gina’s shoulders on late nights. Cucumber and watermelon; the moisturizer sent Rosa delicate hints of spring when winter wouldn’t leave for another six weeks. On lucky evenings, Rosa would perch herself on the edge of Gina’s bed, and Gina would ignore the chips in her manicure as she painted her girlfriend’s nails black. Gina’s sister Amy would kindly turn a blind eye, pressing a finger to her lips before she shyly turned back to her laptop.

 _No one needs to know you’re dating a cop,_ Amy’d insist. _Mom and Dad? They’d throw a fit. So I think you deserve to be happy, and that means keeping your secret for you._

She’d still notice the gold badge tucked into Rosa’s back pocket sometimes, seeing its glint under the light of the ceiling fan. A tad too careless, Amy thought with a frown, to have it out in plain sight. This was a crime family. The Iannuccis traded in white lies and kept each other at a distance, if need be. Amy knew there was no place for liability; her brother Carlo had heard of friends convicted in cases when failing to report made you an accomplice. No give and take, no negotiating, just cut-to-the-bone logic and two types of harsh sentences: those served in prison, and those traded between family members before and after.

Amy knew her sister wasn’t a triple threat. Gina put on a porcelain mask for the public to see: look at the mob boss’ daughter, flaunting her namesake like a fake ID. Watch her every move, is it petty or calculated or an honest mistake, for once? Gina lived a game of nametags, a dimly lit cigarette she hated to smoke caught between the V of her fingers. She’d still let it stain her teeth, just dark enough to show. Anything to fit in. Gina was a spark in a sea of fire, a wannabe Coach purse with a broken zipper passed around between out-of-towners on yet another New York street. Gina was so close to authentic it would’ve fooled nearly anyone, but, at its deepest, her act ran shallow.

Amy loved her sister like vanilla lattes, like celebrating a Christmas, like the inherent joy of closing all 23 open tabs after submitting that last history essay. She loved Gina, the girl who’d taken her in when no one else would. But the common clack of Rosa Diaz’s combat boots made the hairs on Amy’s neck stand up 一 here was the girl who’d rip their family apart if anyone found out. Here was someone else Gina had taken under her gentle wing.

Amy didn’t know if it was jealousy yet. She hadn’t gotten that far before Gina’d whispered in the dark, hopeless and sullen, _how do you know if you’re in love, ames?_

At the time, it’d stung like the rugged sweep of splinter against skin. That was her sister, getting the chance to properly adore someone before Amy’d ever gone on a first date. And with a cop, no less?

Irony laughed at that part.

Irony’d already sent Amy someone to adore, too. He was on his way, too busy letting his career fizzle out to notice a twist of fate unraveling.

**Notes for the Chapter:**

> thank you so much for reading! comments and kudos mean the world to me :)
> 
> 1 comment = 1 sneak-peek at an upcoming chapter!


	3. three

**Summary for the Chapter:**

> _“Okay, so for transactions and inventory, stuff like that, I’m your girl,” Amy announces, walking Jake into her office. “Well, not like I’m your girl,” she stutters, waving her hand as if it’ll clear the air, “I’m not really anyone’s girl-”_
> 
> In which Jake meets Amy, the youngest Iannucci daughter, and Rosa has some revelations about Gina.

Jake Peralta meets the love of his life on a Wednesday afternoon. She’s coaxing a sixty-year-old away from a box marked ‘this side up’ and her lipstick is smudged, but he runs a hand through his oil-slick hair (listen, going undercover doesn’t exactly come with a _dress_ code) and waves hello in spite of it.

“Um, hi? I’m Jake Peralta, I’m starting today. Leo said you guys needed some help with the logistics.” He cocks an eyebrow. Lipstick girl doesn’t seem to notice Jake and he’s too shy to repeat his sentence, so he’s left standing in a warehouse while he twiddles his thumbs.

Leo was one of the NYPD informants. CI #66, to be exact. Terry, Jake’s sergeant, had said it was fun to drop his name every once in a while. Back at the precinct, they held a running tally of how many gangs had taken in a mole without batting an eye because ‘Leo claimed this’ and ‘Leo approved that.’ Jake kept himself company with the humor of this last sentence as he stood by.

“Mrs. Chao, _please_ , be careful! No, don’t lift that!” Amy pats an older woman on the shoulder and beckons her away from the living Tetris game of cardboard boxes. Sighing, she stretches her arms and tucks a few stray hairs behind her ear. “I’m so sorry, you were asking me something. You said something about, uh, Leo?”

“Yeah! Leo recommended me for help with bookkeeping.” Jake isn’t exactly sure how his undercover persona’s facial expressions should differ from his own, so he shoves his hands in his pockets as a half-measure. Coolcoolcoolcoolcool. Nonchalant. For a second, he’s tempted to do finger guns, but he knows better than that.

Amy blinks. “Really? We haven’t heard from Leo in a while. But if you got instructions from him, sure!” She takes a few steps away from the warehouse, stepping toward a hallway carpeted in grey. “Just come this way. What’d you say your name was?”

“Uh, Jake Peralta.”

“Nice to meet you! I’m Amy Santiago,” she says, turning around to shake his hand as she continues her stride toward a back office. The motion is coordinated, Jake notices; the clack of Amy’s heels never quiets as she steps out of line to greet him.

“So what do you do for the Iannuccis?” Jake’s voice echoes between the walls, all chipped brick and worn tile, and he pretends to be comfortable in such an empty place. In training, they never told him about the shivers he’d have to shrug off.

“Well, I’m their daughter.” Amy grins, slipping a key out of an invisible pocket and unlocking a door. She swings it open, beckoning Jake into the room. “Feel free to sit down! And, to answer your question, I keep the books for my family.”

“Oh, good! That’s the kind of work I’m used to, as well.” Jake pulls out a chair, taking note of the office’s trinkets and the lone watercolor by the door. The room seems to scream ‘Marie Kondo’ rather than ‘The Godfather’ like the rest of the warehouse, and his interest is instantly piqued.

Amy takes a seat behind the desk, absentmindedly picking up a snow globe and shaking it. The silvery flakes float and drift in the water, and they catch the light for a moment. She looks down for a moment. “Um, great! Maybe we could work together. I could always use some help organizing spreadsheets or those orderly reports, which take _forever_ and hardly ever pay off in the first place.” 

The NYPD told him not to be too enthusiastic, so Jake bites his tongue. There’s no point in spending months preparing for an undercover mission if you blow your cover on day one, he reminds himself. “Uh, sure?” 

“Oh.” Amy sits up straighter. “Oh. I see.”

Shit, has she caught onto everything already?

“Wait, what?” A cold realization sweeps over him, like a fever after a late night.

“There must be some reason that you’re here,” Amy carries on, beginning to tap her foot against the floor. “I mean, most new guys just show up in the warehouse with my brother Seb, or they go help by driving trucks and making deliveries. I’ve never met someone who wanted to work with _me.”_

Jake gulps. He can hear his blood reverberating in his ears, rushing through every last inch of him. “Amy, listen-”

Using people’s first names can help build trust with them, and he could really use some of that right now. So, under the table, Jake crosses his fingers. Then, like a kid taking a geometry test he’ll never be prepared for, he crosses the fingers on his other hand, too. Eyelash wishes, four-leaf-clovers, anything to make it through.

Amy’s face falls. “Something happened to Leo, didn’t it? That’s why he sent you. Is he hurt? Dead?”

“N-no! He’s fine. I, um, I just begged him to help me find work.” Jake swallows. His knee jerks from below the desk, knocking the wood hard enough to jostle the papers on top. He braces himself as he reaches to readjust everything, his sleeve catching on a corner, and Jake sighs and grits his teeth. Hard, enough to draw blood. “I’m so sorry. Things are kind of rough for me right now. I think I’m on the verge of losing my job.”

“Oh. Oh my gosh, I’ve been so selfish,” Amy says, swallowing her regret. Her hands fly out to reorganize the papers and stack them into a pile. “Here you are, just trying to support yourself, and I’m making all sorts of conclusions about you. I’m sorry. It’s just a, uh, secret code Leo and I made up as kids. In case anything was ever wrong.”

“Hey, don’t worry about it.” Jake smiles. “I’m new, and you got a little bit paranoid. It’s not like you got a job interview before I showed up on your doorstep.”

“Thanks.” Amy pulls a lock of hair away, leaning forward on her elbow. “Really, thanks for being so understanding. I lmean, I just met you.”

“Might as well get to know you, if we’ll be working together.” Jake shrugs. Connect to the Iannuccis on a personal level, his sergeant had said. He feels guilt burrow into him, the way he’s using false pretenses to insert himself into her life. He shakes it off. Remorse resists, then fades. “So, uh, you and Leo knew each other as kids?”

“Yeah, ever since we were eleven. Leo took saxophone lessons with the same guy as me.”

“You play sax, too?”

“French horn,” Amy admits. “Don’t tell my sister I told you, or she’ll show you pictures of my band uniform.”

“Wouldn’t want that. But, completely off-topic, who’s your sister?”

* * *

Rosa Diaz has stuck with the Six-Seven since she began her career in the NYPD. She was younger then, more innocent. (For goodness’ sake, she used to drive a Yamaha, which was basically a step up from a Moped.) In the years since establishing her role as a detective, she’s pulled through all-nighters with a cup of black coffee as her only companion; she’s gone to court and kept her heart from breaking on the stand, confessing in cases she wishes she hadn’t taken. Rosa values silence, and justice, and tequila most of all. Frankly, she’ll need all three to get through her latest assignment.

Rosa tosses back a drink, legs crossed beneath the barstool. She’s seated next to her partner, Dave Majors, and he moves to brush a scuff off her leather jacket but she shrugs it off. She’ll need more tonight than his sad attempts at sympathy.

“So, another smuggling claim against the Iannuccis,” Dave muses, eyeing the half-full glass in his hand.

Rosa grunts.

“It’s drugs this time, y’know.” He leans closer to her. “The charges are getting worse, and we’ll need to do something about their operation soon.”

“That supposed to change anything?”

Dave pauses. “Diaz, I know you’re dating one of ‘em.”

Rosa’s well-practiced in hiding her reactions, and this is no different. Smooth as can be, she buries her surprise beneath a laugh. “ _Excuse_ me? The Iannucci brothers aren’t-”

“It’s not one of the brothers.” Dave’s voice is gentler now, and he looks behind his shoulder before going on. There are conversations trailing off in the background, but nothing of importance. “You and I both know who it is.”

Rosa puts down her glass and turns in her seat. “How’d you find out?”

“I, uh, saw you two together tucked into a corner booth at Wingard’s. I won’t tell anyone, but I just-” Dave purses his lips. “You oughta be careful. Her family’s dangerous, and you might think you can handle yourself, but you’re wrong.”

Rosa looks him up and down. She sees the damn crooked smile that’s got half the patrol officers fawning over him, and the sleek fox tattoo he hides between his fingers (so hipster.) He’s her partner, the highly-decorated-but-refuses-to-brag detective that’s sat across from her for a good four years, and she knows by now to trust his intuition. It’s saved her life before. It could again.

Rosa swallows her pride and says, “I know. I’ll be safe. And trust me, she’s not like the rest of them.”

Majors pauses. “How long have you been together?”

“Uh, about a year. Longer than I should’ve dated her, but she’s just-”

“Hey, I get it.” Dave cracks another smile. “When you know, you know.”

Rosa pays for drinks that night, two twenties gladly spent. She falls asleep alone. Manila file folders litter her bedsheets, detailing the Iannuccis’ latest charge, and they hurt to read. Gina’s name isn’t anywhere on the case, thank goodness, but Rosa can’t help but wonder if it’ll show up someday.

* * *

“Okay, so for transactions and inventory, stuff like that, I’m your girl,” Amy announces, walking Jake into her office. She smooths down her pencil skirt before nudging the door closed with the toe of her shoe. “Well, not like I’m _your_ girl,” she stutters, waving her hand as if it’ll clear the air, “I’m not really anyone’s girl-”

“It’s fine, really.” He nods, doing that raised eyebrow thing that his mother used to call ‘coy.’ (He misses her all of a sudden.)

“Sorry! I’m new to this,” Amy says, forehead wrinkling as she sits down in a worn swivel chair. “I never got to be anyone’s boss before, to be honest.” 

Jake laughs. “No, I get it. And, trust me, I know how it feels to take on a lot of responsibility. You’ll figure it out. So, how can I help? Where do you want me?”

She beams. “Glad you asked.” And as Amy talks, she starts to notice the curl of Jake’s hair, the keen look in his eyes. He leans forward and she can smell his aftershave, all peppermint and soap, and then she’s thinking about the way his forearms look in that grey shirt.

 _And he likes paperwork, too? Hmm, maybe she wouldn’t mind being his girl after all,_ a distinctly Gina-like thought pops into her head. For a moment, Amy sighs, jealous of her sister. Dating a cop with no care in the world about what it means or how it affects you … it must be nice.

* * *

Jake Peralta spends his day buried beneath paperwork in the Marie Kondo room (aka Amy’s office, a shrine to the power of minimalism, positive thinking, and a Staples membership.) Not exactly what he expected from a dangerous, potentially indefinite undercover job, but Amy’s different. Eclectic, in the way you’d describe a handmade card sticking out from between all the carbon copies. He likes it.

Amy, he learns, has had a love affair with lists for years. She gives him sticky notes and Excel sheets, legal pads and bullet-point ideas. (Did he mention he was _buried_ under the paper trail of her plans?) But Amy also makes a point of rearranging the room to bring in a desk for Jake, a chipped white IKEA original with a holographic Pikachu sticker in the left corner.

“Was this originally yours?” Jake asks, looking up at her. He runs a finger over the worn wooden edge, probably rounded after snagging nicks into the shins of people passing by.

“Yeah, sorry! It was the only thing I could find.”

“No, I should say thank you,” he replies. He catches her eye. “Not many people would pull a desk out of storage for a new hire.”

“Yeah, well...” Amy shrugs, “I had a hunch you’d be worth it.”

Jake laughs. “You haven't seen any of my work yet. How d’you possibly know I’ll be helpful?”

“The way you reacted. Not many people would be this grateful.” Amy straightens her back, smiling.

What time Jake doesn’t spend working at his desk, the Pikachu sticker beaming at him, he spends stealing glances of her. Amy’s wearing a collared shirt, and she looks the way that summer feels. She tosses around 90s references, giving pause to see if he’ll get them. Jake spends the remainder of his day fixated on a silver pendant laced around her neck. It’s not his fault, the way Amy keeps biting her lip and readjusting the clasp, wordless and gentle. It’s one of those things you don’t notice about a person until you see them up-close.

Oh, this girl might end up being the death of him. He’s in the middle of the calm before a storm.

**Notes for the Chapter:**

> I want to clarify that this is a work of fiction about FICTIONAL police. It imagines the b99 characters as loving, funny, good people, but those characters are not reflective of the real world, where the police do not serve and they do not protect. Even though everything right now is complicated, I want to say that black lives matter. They always have, they always will, and we need to reexamine our biases before we make any change. I'm not perfect, and I want to be better too.
> 
> Please, if you are able, consider signing petitions, writing emails, donating, attending protests, or educating yourself about the history of civil rights and police brutality across the world. https://blacklivesmatters.carrd.co/ is a great source for this.


	4. four

**Summary for the Chapter:**

> _Amy actually winks, like some sort of charming fever dream wearing smudgy lipstick that he desperately wants to taste, and Jake reminds himself one more time not to ask out the pretty mobster’s daughter._
> 
> Jake has a crush and he can't deal with it.
> 
> Also, CI #10 is making an appearance!

It’s been two months since Jake went undercover, and he’s picked up some tips.

>  **What not to do while undercover with the Iannuccis:**
> 
> Accidentally delete half the hard drive. (Check. Amy was pretty pissed at first, but thanks to her IT genius brother ー David? ー they got the files back.)
> 
> Spill your coffee all over the paperwork (Check.)
> 
> Fall asleep during a shift (surprisingly, not yet. Thank goodness for Jake’s growing coffee addiction, even if he can’t read last week’s quarterly numbers because of the steady cappuccino stains. It looks like the Starbucks mermaid cried all over his reports.)
> 
> Catch feelings for your boss (sadly, check. Jake blames it on Amy’s stupid perfect red lipstick.)

“Hey, are you listening?” She snaps her fingers.

Jake shakes. “Sorry, I, uh, have ADHD. What’d you need?” He feels a little bad pulling the cognitive card, but it’s also a perfect excuse.

“Uh, can you email me the Pedretti file? It’s, like, a scan of their signatures from the business deal we negotiated.”

“Yep, one sec.” Back to the nine-to-five, he thinks, setting his shoulders back after slumping in his wheely chair. You know, the kind that doesn’t end until the sun comes up. Such fun. Capitalism’s a bitch.

At first Jake found the Marie Kondo office kind of pretty, and it was a refreshing change of pace from 12-hour shifts spent at the sterile, brick-laden precinct. Now, he kind of misses the flash of police lights, the glint of his badge. It’s like Amy’s flowery curtains are mocking him, it seems. How can you be so miserable working in an office straight out of Architecture Monthly?

“It’s the file from October.”

“Okay, thanks. October fifth or twenty-seventh?”

Amy takes a swig from her water bottle. She’s a stickler for 8 cups a day ( _hydrate or die-drate!_ ) and she’s only on her third cup but it’s nearly midnight already. “Uh, neither. The Pedrettis’ meeting was on the sixteenth.”

“Ames, I’m really sorry, I don’t see it.” Jake squints at his computer folder, but there’s nothing. Just the steady bluelight of Microsoft Windows.

“But we recovered the hard drive!”

She tries not to appreciate _Ames,_ no matter how cute she finds it. She’s his boss, she’s his boss, she’s his boss. He’s just an employee/friend who slips into nickname territory when his inhibitions have been lowered by sleep deprivation and espresso shots.

“Still empty-handed over here.” Jake groans. Her voice might actually be hurting his head. Can you get a concussion from people talking loudly to you?

“Let me over there.” She leans over his desk, types a few keywords into the search bar. “There we go. You were looking in last year’s files by mistake.”

“Thank you, seriously. Can we please leave now?” Jake turns and shoots a heartfelt look at the door, where his leather jacket hangs next to Amy’s peacoat. “I’m exhausted. I don’t even remember what the inside of my apartment looks like.”

“Uh, that’s because it’s a mess, and there are so many piles of belongings on the ground that you don’t know if you have carpet or hardwood,” she teases. But Amy grabs the keys and pulls her coat off the hook. “Help me put this on? My arms are tired from all that typing.”

“Don’t know why I should help someone who constantly pokes fun at my special cleaning methods.” Jake helps her anyhow, and he tries not to stare when Amy pulls her hair out from below the coat’s collar, tucking it into a messy bun.

Stupid red lipstick.

She shakes her head. “Having a pile of dirty, clean, and in-between clothes isn’t really a special method, is it?”

“You’re so mean, Santiago.” He laughs, sleepy and understated, hair rumpled and eyes dry. He laughs because she can type faster than anyone he’s ever met, and her desk is covered in coupons for grocery stores she promises she’ll start visiting (she’s lying. Amy’s a Whole Foods and Citarella girl only.)

“Pretty sure you haven’t scrubbed the floors in so long that they’ve turned grey from soot and grime.” Amy smirks, adding insult to injury.

“What am I, an English peasant?”

“Well, neither of you have heard of soap or bleach.”

“Keep this up and you’ll lose your star employee, I promise you.” Jake holds the door open for her, and he waits for her to lock it shut.

“Oh dear, I don’t know what I’d do if you quit. I mean, where else would I find someone with the handwriting of a thirteen-year-old boy?” Her voice echoes as they walk down the hallway.

“You’re meannnn.”

“Yeah, but you like me anyways.” And Amy actually winks, like some sort of charming fever dream wearing smudgy lipstick that he desperately wants to taste, and Jake reminds himself one more time _not_ to ask out the pretty mobster’s daughter. (Well, the daughter’s pretty. He’s not so sure about the mobster.)

“Yeah, uh, I do.” He shoves his hands in his pockets, not knowing what else to do with them. “I really do.”

It’s a cold night in New York, with a wind chill so bad that Jake ends up sharing Amy’s green scarf. It’s long enough to drape around both their necks, so they go ahead with the painfully codependent scarf-wearing.

“I swear, I feel so dumb. We look like a married couple in a magazine,” she mutters.

Jake laughs. “We look like a Hallmark movie cover. All we need is pine trees in the background and you clutching a candy cane.” He pats his pocket and groans. “Sorry, I forgot my phone upstairs. D’you mind if we go back for it? I know you’re tired.”

They normally walk home together because, duh, it’s New York. Never mind the fact that he’s literally hanging out with criminals on the daily, but he’d still like to keep muggings to a minimum.

Amy nods. “It’s fine, really. We’ll go back. Besides, if I let you go on your own, I might come in tomorrow and see piles and piles of paperwork all over the floor.”

“I’m not that bad!”

“No, you don’t get it. Your apartment is basically that episode of Friends where Ross dates that professional hoarder.”

“Hey!”

Amy giggles. “Not that I mind. You’re my work husband, so I’m going along with it.”

“I’m your what?”

“Sorry! Sorry. It’s this thing my brother Marco started saying about the two of us because we spend so much time together.” Amy bites her tongue. _Keep walking, keep walking. Avoid future references to any sort of marriage to the cute coworker with the warm brown eyes._

“Nah, don’t apologize. It’s kind of nice,” Jake says, turning to look at her. Her cheeks are pink from the cold, and he reminds himself she’s not blushing on his behalf. He’s not the type of guy to win a girl over. “Never had a work wife before.”

“Well, we had a very good work courtship, so I figured I had to tie the knot,” she teases.

“Ah, yes, I’ll never forget the day I got the job. My whole family was standing there, proud, and the work wedding cake was amazing.”

Amy smiles, because Jake was twenty-four before he learned that cousins twice removed haven’t actually been exiled from the family. Because Jake’s favorite food used to be frosting, and he wants a lemon-blueberry-goaheadsurpriseme cake if he ever gets married.

Jake whimpers a little as he opens the door to the stairwell. “Take my hand and drag me back to our office, work wife?”

“I’d be honored.” She does a little imaginary sweep-my-dress-aside thing, looping her arm in his, and her heeled boots clack as they move.

There’s this funny thing about walking up stairs, where the first two flights are fine yet, by the third, your hamstrings are begging for mercy. (Title of your sextape.) The Marie Kondo Sanctuary is three flights up, so Amy heaves for breath outside the door and hands Jake the keys.

“Go ahead, I’ll wait out here.”

Jake walks in to grab his cell phone, left on the desk or something, and he swipes a glance at Amy’s computer.

Okay, good. He’d left the phone there on purpose, after noticing Amy hadn’t shut her laptop like she normally does. Blame the midnight shift, it hadn’t crossed her mind. Jake opens her files, pulls a few open, and takes photos of anything suspicious.

_Enclosed:_

_Please find notice of your new position._

Jake frowns. That could mean anything. He clicks the email attachment, but nothing pops up. Must be some sort of self-destruct safety function, which is a red flag on its own.

_Dime here, sent the latest report out @1800. Pickup is the place we used last last last time, k?_

A knot settles in his stomach, thinking Amy ー Amy who can’t bear to shoplift produce, Amy who apologizes at airport security when her enamel pins trigger the metal detector ー she might be in deep. Smuggling, maybe. Robbery? Or it could be drugs, the Iannuccis had a history of moving prescription meds under the counter.

This could be bad.

This is why they teach you not to catch feelings for your boss, no matter how cute she is when she loops her scarf around her neck.

But it’s his job, so Jake swallows and takes a picture anyways. Never mind how invasive this is, and how hurt Amy would be if she knew he was in there going through her stuff.

* * *

_[messages, 12:12 am]_

**dave majors:** Hey, we gotta talk.  
**dave majors:** Just got some news from my undercover stint. Things are looking really different.

 **rosa diaz:** How different?

 **dave majors:** Shouldn’t tell you over text. See you before work?

 **rosa diaz:** course.

* * *

What in the world was Dime?

And what was 1800, a place? A time? A year? Some other stupid code that Amy’s genius brain came up with?

(Okay, wrong time to wax poetic about how smart his friend was.)

The pictures on his phone felt like they’d burn a hole in his pocket. He was a thief, not quite red-handed but just as guilty.

“Hey! Took you long enough,” Amy says, tapping at her watch outside the office.

“Sorry ‘bout that! My phone was nearly dead, I had to charge it inside.”

“No problem. It was a nice break before heading home, and I actually got some work done, too.”

Jake rolls his eyes. “Workaholic. Give a rest, would you?”

* * *

_[messages, 12:14 am]_

**CI #10:** what r we doing next??

 **dave:** Nothing. We’re laying low.

 **CI #10:** i dont like sitting still  
**CI #10:** feels like everythings off

 **dave:** just relax! dance around. go to the park. go to Whole Foods or Citarella and buy a $12 bag of organic quinoa. I know you, 10.  
**dave:** enjoy the silence while you have it.  
**dave:** no need to be so type A :)

 **CI #10:** k

Like Amy had said, she’d gotten some work done while Jake was getting his phone.

**Notes for the Chapter:**

> hi, I hope you enjoyed it! Ended up falling into a rabbithole and writing this chapter in one sitting.
> 
> Comments/kudos are greatly appreciated Anyone who comments will get a line from a draft or future chapter of this fic!


	5. five

**Summary for the Chapter:**

> Then again, lucky people usually didn’t catch feelings for gamblers’ daughters. It was part of the picturesque Hallmark movie-ness of it all. This felt more like The Godfather.

“Majors! What’d you want to talk to me about?” Rosa asks.

“Yeah, just a sec.” Dave looks up from a phone call, then puts it away. “Sorry, an old friend was calling me. Anyways, it was about the smuggling cases from the Iannuccis. My CI’s been telling me they’re prepping a big shipment soon.” As he talks, he picks at his tattoo, a running fox inked on the skin between his fingers. Nervous habit.

“How soon’s the shipment coming in?” she demands.

“Uh, two weeks? I’m not sure. My CI’s saying they’ll probably need all hands on deck, so, um … more of the Iannuccis might be involved this time.” Dave paused, like ‘just reminding you, that one girl you’re in love with may or may not be implicated in this illegal act.’

Rosa nodded. “Thanks, Majors. Anything specific we should do for the taskforce?” Their precinct, the Six-Seven, was closest to the Iannuccis’ turf. They’d set up a taskforce to monitor the family.

“The captain’s saying we could stake their family out soon. Tomorrow night, you up for it?”

Rosa thought ahead. She and Gina didn’t have plans until the end of the week, drinks at Wingard’s, same as always. “Tomorrow works. See ya then.”

It was starting, wasn’t it? The beginning of the end when it came to her & Gina. Rosa felt a pit in her stomach, but she pretended it wasn’t there. It was easier to stay afloat when you didn’t see the leaks in your ship. At first, that is.

* * *

“Ames, I’m telling you, you picked a keeper,” Gina says, leaning over the bar and fiddling with the olive in her martini. “How’d you manage to find a cute guy who likes paperwork? I mean, ‘likes paperwork’ is code for nerd glasses and science camp every summer.”

“I happen to know that you loved science camp,” Amy murmurs. She looks up from her drink to see her sister’s jaw clench. It’s a subtle motion, just like the rest of her.

“You came in second place during the toothpick castle contest,” Amy continues.

“Ames!”

“The medal’s hidden in your dresser at home because you don’t want to let go of it.”

Gina kicks her shin beneath the counter. “Just ruin my reputation in one fell swoop, hmm? Anything else you wanna spill while the box is open, Pandora?”

“Nah, I think I’ll save it for next time.”

Amy sips her Cosmopolitan, content to have the upper hand, until Gina mutters, “Fine, I’ll let you get away with it. Don’t think I don’t notice you avoiding the idea of dating Peralta.”

“We’re friends.”

“He’s _so_ your type. Funny, geeky, clumsy, cool in that barely-there way … what are you waiting for?”

Amy turns around, checking out the patrons at Wingard’s as if Jake has materialized within the last 5 minutes, and then she leans in. “I’m his boss, okay? I hired him. I trained him. And I don’t want to mess up a good thing if I get all emotional and ask him out.”

“But he clearly likes you!” Gina protests. “When’s the last time you liked someone this much?”

Amy frowns and swirls the black straw in her drink, letting the ice clink like marbles against the glass. “It’s all in my head. He’s like my best friend.”

Gina rolls her eyes.“Excuse me, aren’t _I_ your best friend?”

“Well, then, he’s my second-best,” Amy says. “But you’re my favorite.”

“Gina Iannucci regains the throne once more, ladies, gentlemen, and nonbinary crowd members!” She drinks the rest of her martini and carves a jagged smiley face into the olive using a toothpick.

The night follows them smoothly, follows their empty glasses and dizzy heads until the sisters hail a rain-soaked cab and step inside. Gina’s heels drag along the floormats, and Amy giggles something to the driver about Gina’s silver summer-camp medal. When they arrive home to their apartment building, Amy pushes the wrong button on the elevator and they spend a good two minutes wrestling with their key in someone else’s door. Gina realizes, slaps her sister’s hand away, and they just about die laughing.

Amy falls asleep at 2 AM, still wearing her dress and smeared makeup.

She doesn’t notice the text on her burner phone from Dave Majors, saying he needs her to send in more reports next week. She doesn’t realize that Jake’s sent her two puns about squirrels. All she does is see darkness, bouncing off the insides of her eyelids for eight hours straight.

Gina sends goodnight emojis to Rosa and crawls into bed, shedding her stilettos on the way back from the bathroom. She, too, fails to notice her phone. It’s a first for her. Usually Gina and iMessage are inseparable.

_[messages, 2:39 AM]_

**rosa:** hey, we should talk sometime. Nothing serious, not like a breakup thing. I have something important to bring up. It’s a good thing, don’t worry.

* * *

**The thing about gambling no one tells you:** you’re supposed to win often, but never a lot. At least not in one fell swoop, like lottery-award _I never need to work again_ winning. While you might get away with small and infrequent successes, the flashier rewards only make you seem ingenuine. People pick up on your tells, or lack thereof. They spread rumors about trick decks and hidden cameras.

The thing about gambling you’ve probably already guessed: when you’re undercover, you get pretty used to that ingenuity. That’s just the way the cards fall.

Jake Peralta’s been undercover for about three months now. By day, he’s a bookkeeper alongside Amy. By night, he’s been learning to gamble: poker, blackjack, war, even something called baccarat that’s starting to get popular in Brooklyn. And gambling _sucks,_ you should know, when you’re someone in his position. Either you’ve got someone on the inside helping you and you’re looking over your shoulder at every chance, hoping none of your opponents figures it out, or you actually have to be a good gambler.

Jake was not a good gambler.

“Game over!” Detective Boyle said. He chuckled, kicking his legs up like he wanted to jump out of his chair.

“Again, really?” Jake threw his cards on the table and they landed half-up, half-down.

“I hate to say this to a decorated police officer, but you haven’t won in six rounds.”

“Thanks for reminding me, Boyle,” Jake said. It was late, his bones were sore, and he could feel the losses in each of them. He had to play the Iannuccis soon, yet most of his practice time had been absorbed with Amy and the Marie Kondo office. This was generally because he was her employee, mostly because it’d be suspicious if he weren’t available, and slightly because he had a crush on her.

It wasn’t going to go anywhere, Jake knew, much like his sad poker-playing career. In the best of situations, having a crush on your boss led to secret relationships, then telling HR, then a proposal if you were really lucky. Then again, lucky people usually didn’t catch feelings for gamblers’ daughters. It was part of the picturesque Hallmark movie-ness of it all. This felt more like The Godfather.

“So what are our options now?” Jake asked Holt, whom he hadn’t seen in a while. The captain was a gambling addict, and he knew his limits very closely. He’d sighed and given in, though, after hearing Boyle’s report about Jake’s skills.

“Easy,” Holt said. He didn’t say that word very often. “We set you up with an earpiece and camera, and I play the game on your behalf. I’ll make the choices, if that’s alright.”

Jake grinned, a real _now I remember what my old life was like-_ type grin. “Sounds like a plan. Can I go now?”

Boyle nudged him. “Leaving so soon?”

“I’m essentially working two jobs-” Jake yawned, continuing after his voice came back to normal. “And neither of my employers would be fans of the other.”

“Really, Amy Iannucci wouldn’t approve of you working with the police?” Holt asked. “She’s known for coloring inside the lines. She doesn’t even gamble.”

“It’s Santiago, sir.” Jake yawned again, stretching in his seat. “And trust me, I know her better than you think. She might have a clean record, but her brothers don’t.”

“Alright, then, Peralta.” Holt stood up. “Goodnight.” He and Boyle left the warehouse.

It was hard to accept that Jake knew much more about Amy than she knew about him. Amy got the good sides of Jake, flannels and fruit snacks and terrible puns. Jake got more than that. He’d read her file, learned about her birth parents (couldn’t support her) and the adoptive ones (dead. Technically, they also couldn’t support her.) He knew about her brothers even if he’d barely met them in person.

Jake had the up-close Amy and the police-files Amy and the Amy in the newspapers and the Amy that every other person talked about: Gina, Captain Holt, Detective Boyle, Sergeant Jeffords. It was terrifying to consume about ten different reputations of her and build an idea of her in his head. It was scarier still to love up-close Amy the best. Up-close Amy was much better at being a person than up-close Jake, because she was put-together and rational while Jake routinely sang terrible songs like _Barley and Jimes_ and waxed poetic about every individual Die Hard cast member.

Not to add insult to injury, but police-files Amy (clean record) was also a much better person than police-files Jake (fell in love with an Iannucci during his stint investigating their family, once arrested a guy’s twin brother instead of the real suspect, misfiled evidence three times, has cried on the stand in front of a very awkward jury 一 the attorney was being mean! 一 and many, many counts of bad handwriting and goofing off during stakeouts.)

But mainly, the falling in love part was the worst crime, because it was ongoing. You can apologize all you want for something that happened, because you can go with ‘I’m a better man now’ and ‘I was lost! I was confused!’ When something is still happening, not so much.

Jake texted Amy two puns about squirrels and fell asleep. 2:39 AM, and he dozed off dreamlessly.

* * *

Gina Iannucci is sort of immune to hangovers. Her sister and her girlfriend both hate her for it in different ways. Amy tends to go all “just because you don’t feel bad doesn’t mean you’re not hurting yourself! You should stop drinking so much!”

Rosa’s more of a “sweeeeet, why aren’t we all wired like you are? teach me thy ways” person.

Gina wakes up the next morning to Rosa’s text, and she feels a little guilty for reminiscing about good memories. Gina’s last name gave her prestige, yes. It also made her vulnerable. Regular people could get a date on Bumble or Tinder or Hinge or, if they were really desperate, by asking someone out on Facebook.

(Note: never, _ever_ ask someone out on Facebook because you once had a blind date set up and then you cancelled it and now you’re wondering if the other person is still interested. This is the worst dead-end road you will ever drive down.)

Anyways, when your family had notoriety, it wasn’t so easy. You had to be cooler than everyone, less needy, and putting on airs only made it harder to find anyone. It was a miracle that Gina had run into Rosa at Shaw’s and struck up a conversation.

When you were an Iannucci, dating someone worthwhile was _hard._ Not to cry alligator tears and pull the “I’m a celebrity” card, but, in certain circles, that’s exactly what they were. Iannuccis were richer, they were fouler, they were more cutthroat, they were unintelligible. There was a family saying in Italian, something about good workers moving like ants in a hill. They knew where they were going and, if they were smart, nobody else had a clue.

Gina felt awfully ant-like, waiting for Rosa to text back. Their relationship was going somewhere, but no one outside of Gina and Rosa (and Amy) knew anything about it.

* * *

Amy Santiago had never been on a real date. There had been the stressful disaster of asking Teddy out (on Facebook! Like an idiot!), only because her brother knew him as a friend of a friend and, to put it mildly, she was lonely. They’d set up a date, and then Amy backed out at the last minute, and then spent a year wondering if Teddy was actually nice and, slowly, worked up the nerve to ask Teddy out on a second first date. He said yes.

This was a dead-end road because Teddy was (A) boring, (B) cracked a couple douche-y jokes, and (C) decided that they were going to make pilsners because, if he liked pilsners, of course she would, too! Typical guy. Terrible listener.

Of course, Amy didn’t know that yet. Facebook Messenger Teddy was a harmless first date. He looked great on the outside, and that greatness shone through as Teddy and Amy discussed their tastes in music and books.

In-person Teddy was not harmless. After choking down a weird brine-y beer drink (‘that’s what pilsners taste like!’ Teddy insisted) and sitting through his rant about coupons, Amy had ghosted Teddy and ghosted Facebook altogether. He’d seemed so nice online. People are much better when you get the Facebook Messenger version of them.

So, technically, Amy’d been on a date, but not a real date. She liked to think that her first actual date would be with someone much better than a boring, mansplaining, pilsner-making guy. Maybe with Jake! Maybe with her soulmate. Who knew? Amy enjoyed the relative anonymity of not having Iannucci as her last name. She lived without the burden that any first date would eventually hear about the … family business. Better to say that than ‘smuggling ring.’

Sometimes Amy really wished she could be brave and ask Jake out. But she’d gone down that road with Teddy, and it’d soured her on the concept of asking for dates unconventionally. She didn’t even know how to ask for dates conventionally!

Here’s the thing about dating: everyone acts like it’s supposed to happen when it happens, but no one leaves room for the people that just… don’t have anything happen to them. No one scrawls down their phone number or develops an uncanny crush that fits perfectly into a movie. You just go through life unskilled in the art of first dates, waiting to be asked on one. (I’m aware that Amy has a love interest in this story, but she is unaware so far. It’s very hard to feel normal when nothing is happening to you and different people shrug it off with ‘you’re not putting yourself out there!’ or ‘be patient.’)

Amy was being patient, and she thought she was putting herself out there.

She replied to Jake’s texts with a squirrel pun of her own, she rubbed her eyes, she tried to stop cringing at the thought of her one terrible, poorly-sought-after first date, and she got out of bed.

* * *

Rosa came over to Amy and Gina’s apartment shortly afterward.

She sighed, tucking her motorcycle keys in her coat pocket. She walked to the kitchen table and tossed a glance at Amy’s bedroom door, closed. “I’m really sorry. I don’t know how to put this politely, so I’m just going to say it. I think we should spend some time apart, just for investigative police reasons. It’s not about you and me, it’s about a detective and an Iannucci.”

“That was very put-together. Have you been practicing?” Gina asked.

Rosa smiled. “All morning, especially during the drive here.”

“So we’re not breaking up.”

“I don’t wanna break up. You’re the only person I’ve ever dated who also hates soup.”

Gina’s brow furrowed. “Surely my likability extends beyond my dislike of soup.”

“Well, you’re good in bed too,” Rosa shrugged. Jokes were good, they showed comfort. “I’m really sorry, but I think we should quit spending so much time together publicly. I don’t want to get pulled into the drama of-” she waved her hand around, like that’d explain organized crime and family ties. Duh! “The drama of those police investigations involving your brothers.”

Gina nodded. “I get it. I don’t like to get involved in their business, but I also don’t want to get exposed or whatever by the police. Your reputation and mine are too distinct and important to mess with.” She held Rosa’s hand from across the table. “In your circles, you’re cold and honorable. In mine, I bend the rules.”

“I know it’s gonna be really hard,” Rosa says. “I think we can still text and call, and I can come to your place and you can visit mine. But it might last a long time. There are a lot of police cases involving your family.”

Gina scoffed, but not in a rude way. She was laughing at Emily Goldfinch, the artificially sweet persona Rosa had built and used and set aside for the four walls of her apartment building. “So, a lot more time as Emily, huh?”

“It’s kinda fun playing a role. You get used to it. I’m Emily Goldfinch and you can be…”

“Ooh, Beyoncé Knowles!”

“A less obvious name, please.”

“Katerina Maple.”

“Okay.” Rosa leaned in for a kiss. “And we’re not breaking up?”

“Nah, I like you too much.”

* * *

_[messages, 1:29 PM]_

**jake:** do you ever wonder why we’re here in the universe?  
**jake:** I hate to sound like a nutcase u know  
**jake:** I just have this feeling like there’s a reason why we’re so bright-eyed and bushy-tailed  
**jake:** why we live for the chase  
**jake:** why we store nuts for the winter

 **amy:** please stop with the bad (and existentialist?) puns  
**amy:** I was attacked by a squirrel in my backyard ONE TIME  
**amy:** I regret telling you this story

 **jake:** I’m never letting you live this down  
**jake:** Gina sent me pictures of you during your squirrel attack  
**jake:** IMG_3890.jpg

 **amy:** well, now Gina and I need to have a talk  
**amy:** Okay, if I let you keep teasing me about this, I get to know one embarrassing thing about you

 **jake:** deal  
**jake:** my grandma used to call me pineapples :///

 **amy:** why?

 **jake:** one time I asked her why pineapple vines don’t grow in New York and she laughed for 10 minutes straight before explaining THERE ARE NO PINEAPPLE VINES  
**jake:**...I was seventeen

 **amy:** your new contact name in my phone is Pineapples Peralta  
**amy:** gone is the era of Jake, long live pineapples

* * *

_Deep breath. Sly look. Deep breath again. Think less ‘geeky high-schooler’ and more ‘overrated white celebrity who just won an Oscar, now he’s heading to the afterparty.’_

There are two Iannuccis by the front door, and there’s another guy at his table tonight. Jake approaches slowly, trying to act like his tie isn’t strangling him. He doesn’t have to be a good gambler, he has Holt as his eyes and ears. Deep breath. Sly look. He’s got this.

“Hey, Peralta.” A guy in a leather jacket beckons him over with a swoop of his fingers. His voice is gruff. “Glad you could make it.”

“You been expecting me or something?” Jake cocks an eyebrow.

He shrugs. “Word spreads when a cop shows up to poker night.” The guy extends his hand. “I’m Leo, Amy told me about you.”

“She talks about me?”

“A little bit. She said you were in the police, that’s all, and you were thinkin’ of leaving. Oh, and she said you worked with her.” Ah, the good old NYPD-provided cover story. Leo goes on. “I’m kinda in the same boat, job-wise, so I just wanted to introduce myself.”

“Oh, okay.” Jake keeps his expression still. How nice are gamblers supposed to be? “Uh, thanks for letting me know. Nice to have people who can sympathize. I’m Jake. Nine-Nine.”

“Nice, I’m over at the Six-Seven.” Leo cracked his knuckles, showing off a tattoo between his fingers for just a second. He turned toward the door as the bell jangled above. “Hey, look who finally turned up. Now it’s getting interesting.”

A brunette in a dark coat was shrugging the fabric off her shoulders. Two different men were trying to help her out of it, but she just cracked her gum and ignored them.

“You know her?” Jake asked. There weren’t many women who’d shown up to poker with the Iannuccis. With a family as large as theirs, every brother had brought a friend, and the room was beginning to fill.

“Everyone knows _of_ her, they just don’t know her,” Leo murmurs. “Gina Iannucci, best of the best.”

She walked by their table slowly, boots clacking on the floor until she reached red carpet. Her table was smaller than theirs, the chairs more tightly packed. When you were with the in crowd, your guest list thinned. You didn’t need onlookers. You worked in silence, not applause.

Jake frowned. “You don’t know Gina? You’re friends with her sister.”

“Amy’s not really an Iannucci like her sister is, you know? She runs behind the scenes, not on the stage. She didn’t grow up influenced by their parents,” Leo says. “Her family loves her. They just don’t understand her sometimes.”

“No wonder she picked the last name Santiago.” Jake wonders how hard it’d been for Amy, navigating that new terrain, but he doesn’t let the thought color his tone. This is police-files Jake, not the up-close one. He didn’t have time to be sensitive.

“Yeah. I mean, no disrespect to adopted kids, but she doesn’t look like ‘em and she doesn’t gamble, she doesn’t speak their language. Of course you’re gonna have trouble fitting in.”

Jake spends his night playing poker, Holt’s voice in his ear. He keeps a close eye on Gina’s table, sequestered in a corner. This’ll be a long night. The Iannuccis are like fire ants, someone at the precinct once told him. When one bites, the others latch on. But before then, they stir and plan and wait for a target to cling to.

Jake was fairly sure he might end up their target. Crime families weren’t especially keen on cops living a double life, were they?

 _Peralta, pay attention,_ Holt said over the earpiece. _Now take the two queens and the king…_

* * *

Leo gulped. Shouldn’t have mentioned working at the Six-Seven, and he definitely shouldn’t have struck up a conversation about the Iannucci girls. Jake might be trustworthy because he worked with Amy, but you never know.

Leo hoped Jake hadn’t met him at some convention or training session years ago. It happened from time to time. That was just life when you had two first names, interchangeable, mix-and-match.

His name was Dave, too. Dave Majors.

Leo never meant to trick anyone, really. He met Amy in foster care when they were in elementary school. She was adopted by the Iannuccis, and then the Majors took him in. (Majorses always sounded weird.) His parents were good, but he spent more time with Amy’s family as he got older. He was an only child, and the Iannucci brothers were so inviting.

Inviting until he was sixteen and shoplifting, seventeen and smuggling carts of _I don’t even want to know what_ past security, eighteen and technically too old for juvie, nineteen and trying to whitewash his record, twenty and convincing the NYPD that his background could be used for good. He was twenty-one and changing his name and going undercover, twenty-two and undercover, twenty-three and undercover … twenty-eight and living two different lives.

Playing poker with the Iannuccis was undercover work, too. It never stopped, it burned him out, it drove him places he hated going. Leo remembered the taste of the cigarettes he was required to smoke. He had scars that went deeper than skin allowed. When people got used to the idea of him, he could never give them the full picture. It was so much easier to bail than to explain the mess he’d made on purpose.

Amy knew about the arrangement, but she didn’t tell anyone. Sweet, put-together Amy, just sitting in her office and pushing paperwork for her family. Briefly, Leo wondered how nice it must’ve been to live one straightforward life. No lies, no worry, no ducking for cover. He wished he could have her job sometimes.

No one else got to know that Leo and Dave were one and the same. And, certainly, a cop from the Nine-Nine who gambled when he should’ve been upholding the law? Jake Peralta couldn’t learn a word of this.

**Author's Note:**

> thank you so much for reading!! I've been obsessed with this idea for a few months and I really love it
> 
> comments and kudos are always appreciated! anyone who comments will get a one-line preview of an upcoming chapter :)


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